CN1764451A - The preparation method of 5-methyl-N-(methyl aryl)-2-ketopyrrolidine, 5-methyl-N-(methyl cycloalkyl)-2-ketopyrrolidine and 5-methyl-N-alkyl-2-ketopyrrolidine - Google Patents

Abstract

The present invention relates to utilize metallic catalyst, by prepare the method for 5-methyl-N-(methyl aryl)-2-Pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone and 5-methyl-N-alkyl-2-Pyrrolidone with aryl cyano compound reduction amination levulic acid, described metallic catalyst is optional to be on the carrier.

Description

The preparation method of 5-methyl-N-(methyl aryl)-2-Pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone and 5-methyl-N-alkyl-2-Pyrrolidone

Invention field

The present invention relates to utilize metallic catalyst, by preparing the method for 5-methyl-N-(methyl aryl)-2-Pyrrolidone, 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone and 5-methyl-N-alkyl-2-Pyrrolidone with aryl cyano compound reduction amination levulic acid, described metallic catalyst is optional to be metallic catalyst on the carrier.

Background of invention

As everyone knows, levulic acid is the saccharinic acid hydrolyzate, can be obtained by cellulosic material at an easy rate.Therefore, it is the many 5 useful carbon compounds of preparation and the attractive raw material of derivant thereof.For example, as solvent or intermediate, described commercial Application comprises electronics industry (photoresist demoulding solution), industrial cleaning agent, oil/gas well maintenance and stock-dye to N-cyclohexyl-2-Pyrrolidone in many commercial Application.The N-[2-ethoxy]-2-Pyrrolidone can be used for industrial cleaning, printing-ink and gasoline and oil additive.N-octyl group-2-Pyrrolidone in agricultural product are made, as abluent and dispersant, in industry and metal cleaner, is useful at printing-ink with in stock-dye for example.

United States Patent (USP) 3,337,585 disclose, and 50 ℃ to 350 ℃ temperature, the carbon monoxide atmosphere downforce is 1.0 to 101MPa, utilizes levulic acid and kiber alkyl amine to prepare the method for 5-methyl isophthalic acid-alkyl-2-Pyrrolidone.Other potential primary amine comprises Alkylenediamine, arylamine and Cycloalkyl amine.Do not use nitrile (alkyl cyanide based compound).United States Patent (USP) 3,235,562 have described the vapor-phase process by reduction amination oxo carboxylic acid compound lactams.Can use volatility alkyl or aryl primary amine; Do not use nitrile.Candeloro and Bowie (Aust.J.Chem., 1978,31:2031-2037) described, by the prepared in reaction 5-methyl-2 between levulic acid and the aniline under nitrogen atmosphere, 3-dihydro-1-H-benzo-aza _-method of 2-ketone and 5-(2-methyl-5-oxo-1-Phenylpyrrolidine-2-yl)-4-oxo-N-phenyl pentanamide.

A kind of efficient and cheap method for preparing aryl, alkyl and cycloalkanylpyrrole alkane ketone will be favourable.

The invention summary

The present invention is in the presence of catalyst, and levulic acid or derivatives thereof and cyano compound are converted into aryl, a kind of novel one-step method of alkyl and cycloalkanylpyrrole alkane ketone, and this method will be discussed in more detail below.Specifically, the present invention relates to prepare the method for 5-methyl-N-(methyl aryl)-2-Pyrrolidone (III), 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone (IV) or its mixture, it is included in catalyst and hydrogen and exists down, the step that chemical compound levulic acid (I) is contacted with aryl cyano compound (II);

Wherein, R ₁Be aryl with 6 to 30 carbon atoms, R ₂Be R ₁All or part of reductive deriveding group, and wherein 5-methyl-N-(methyl aryl)-2-Pyrrolidone (III), 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone (IV) or its mixture can constitute the 100wt% of formed gross product, perhaps wherein can produce other product.

The catalyst that is useful on the inventive method is to be selected from palladium, ruthenium, rhenium, rhodium, iridium, platinum, nickel, cobalt, copper, ferrum, osmic metal, their chemical compound and their combination.

The invention still further relates to the method for preparing 5-methyl-N-alkyl-2-Pyrrolidone (VI), it is included in catalyst and hydrogen and exists down, the step that levulic acid (I) is contacted with alkyl cyanide based compound (V);

Wherein, R ₃Be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀The alkenyl, the C that do not replace or replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀The cycloalkyl that does not replace or replace or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace; And wherein 5-methyl-N-alkyl-2-Pyrrolidone (VI) can constitute the 100wt% of formed gross product, perhaps wherein can produce other product.

The catalyst that is useful on the inventive method is to be selected from palladium, ruthenium, rhenium, rhodium, iridium, platinum, nickel, cobalt, copper, ferrum, osmic metal, their chemical compound and their combination.

Detailed Description Of The Invention

" levulic acid " expression has the chemical compound of following formula:

" aryl cyano compound " expression has the chemical compound of formula R-CN, and wherein R is an aryl.

" 5-methyl-N-(methyl aryl)-2-Pyrrolidone " expression has the chemical compound of following general formula, wherein R ₁Be aryl with 6 to 30 carbon atoms:

" 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone " expression has the chemical compound of following general formula, wherein R ₂Be cycloalkyl with 6 to 30 carbon atoms:

" 5-methyl-N-alkyl-2-Pyrrolidone " expression has the chemical compound of following general formula, wherein R ₃Be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀The alkenyl, the C that do not replace or replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀The cycloalkyl that does not replace or replace or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace:

" catalyst " expression influences reaction rate but does not influence molecular balance and chemical unchanged material before and after chemical reaction.

" metallic catalyst " expression is by at least a metal, at least a catalyst that draws Buddhist nun (Raney) metal, its chemical compound or combinations thereof.

" promoter " expression adds the element of the periodic table of elements of the physics improve catalyst or chemical functional.Promoter can also add suppresses disadvantageous side reaction and/or influences reaction rate.

" metallic promoter agent " expression adding improves the physics of catalyst or the metallic compound of chemical functional.Metallic promoter agent can also add and suppress disadvantageous side reaction and/or influence reaction rate.

" all or part of reductive deriveding group " expression of aryl compound is by the one or more unsaturated bonds on saturated or the reduction aromatic ring, by the parent compound derived compounds.Unsaturated compound is to contain one or more carbon-carbon double bonds or triple-linked chemical compound.For example, the deriveding group of the Restore All of phenyl is a cyclohexyl.

The present invention relates in the presence of catalyst and hydrogen, by the synthetic 5-methyl-N-(methyl aryl) of the reaction between levulic acid (I) and the aryl cyano compound (II)-2-Pyrrolidone (III), 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone (IV) or its mixture;

Wherein, R ₁Be aryl with 6 to 30 carbon atoms, R ₂Be R ₁All or part of reductive deriveding group, and wherein 5-methyl-N-(methyl aryl)-2-Pyrrolidone (III), 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone (IV) or its mixture can constitute the 100wt% of formed gross product, perhaps wherein can produce other product.

The invention still further relates in the presence of catalyst and hydrogen, synthesize 5-methyl-N-alkyl-2-Pyrrolidone by the reaction between levulic acid (I) and the alkyl cyanide based compound (V):

Wherein, R ₃Be alkyl with 1 to 30 carbon atom, and R ₃Can be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀The alkenyl, the C that do not replace or replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀The cycloalkyl that does not replace or replace or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace; And wherein 5-methyl-N-alkyl-2-Pyrrolidone (VI) can constitute the 100wt% of formed gross product, perhaps wherein can produce other product.

Can contain in the inventive method on the carrier or be not that supported catalyst is to influence aminating reaction.Can randomly use promoter to come assisted reaction.Promoter can be metal.

The inventive method can with in batches, preface criticizes (being a series of batch-type reactors) or continuation mode, in the commonly used any apparatus of continuous process (for example, referring to H.S.Fogler, ElementaryChemical Reaction Engineering, Prentice-Hall, Inc., NJ carries out in USA).For example distill by the separation method that adopts usually in this separation, remove the condensation water that forms as product.

Formula (II), (III) and (IV) in, R ₁And R ₂The aryl and the cycloalkyl of expression preferably have 6 to 30 carbon atoms.More preferably, formula (II), (III) and (IV) in R ₁And R ₂The aryl and the cycloalkyl of expression have 6 to 12 carbon atoms.The example of formula (II) preferred embodiment is the benzene nitrile; Therefore formula (III) and (IV) can be respectively 5-methyl-N-benzyl-2-Pyrrolidone and 5-methyl-N-(methylcyclohexyl)-2-Pyrrolidone.In formula V or the formula (VI), R ₃The not replacement of expression or substituted alkyl or cycloalkyl preferably have 1 to 30 carbon atom.More preferably, in formula V or the formula (VI), R ₃The not replacement of expression or substituted alkyl or cycloalkyl have 1 to 12 carbon atom.

In the inventive method, during the reaction beginning, the mol ratio of cyano compound and levulic acid or its salt is preferably about 0.01/1 to about 100/1.Mol ratio more preferably about 0.3/1 to about 5/1 during the reaction beginning.

The temperature of the inventive method be preferably about 25 ℃ to about 300 ℃ scope.More preferably, for about 75 ℃ to about 200 ℃ temperature range.

The pressure that the inventive method adopts is that about 0.3MPa is to about 20MPa scope.Be preferably about 1.3MPa to about 7.6MPa pressure limit.

The present invention's reaction can be carried out in non-reaction dissolvent medium such as water, alcohol, ether and ketopyrrolidine.In addition, excessive aryl or alkyl cyanide based compound also can be used as solvent medium.

Useful catalysts of the present invention is to influence reaction rate but do not influence molecular balance and chemical unchanged material before and after the chemical reaction.Chemical promoter has increased activity of such catalysts usually.Promoter can combine with catalyst in the arbitrary steps that the chemical treatment catalyst is formed herein.Chemical promoter has promoted the physics or the chemical functional of catalyst usually, suppresses disadvantageous side reaction but also can add.

The inventive method relates to aryl or alkyl cyanide based compound reduction amination levulic acid, and it carries out in the presence of catalyst.The main component of useful catalysts is to be selected from palladium, ruthenium, rhenium, rhodium, iridium, platinum, nickel, cobalt, copper, ferrum, osmic metal, their chemical compound and their combination herein.

Can randomly use promoter in the present invention's reaction.Promoter can combine with catalyst in the arbitrary steps of chemical treatment catalyst component herein.Be applicable to and be selected from the metal of stannum, zinc, copper, gold, silver and their combinations promoter the comprising of the inventive method.Preferred metallic promoter agent is a stannum.Operable other promoter being is selected from the element of periodic table of elements I family and II family.

The catalyst that uses in this method can be on the carrier or not at supported catalyst.Supported catalyst is the catalyst that obtains through following method, described method comprises active catalyst is deposited on the carrier material by several different methods such as sprinkling, immersion or physical mixed, subsequent drying, calcining, if desired, by method activation as reduction or oxidation.Usually the material as carrier is the high porosu solid of total surface area (external surface area and internal surface area), and this porosu solid can make the catalyst of Unit Weight have the active sites of high concentration.Catalyst carrier can improve the function of catalyst.Metallic catalyst on the carrier is that wherein catalyst is the supported catalyst of metal.

The catalyst that is not supported on the catalyst carrier material is non-supported catalyst.Non-supported catalyst can be platinum black or draw Buddhist nun (Raney) catalyst.Term used herein " La Ni (Raney) catalyst " but be meant owing to the selectivity drop goes out to contain the catalyst that alloy that reactive metal and drop go out metal (normally aluminum) has high surface area.Any special source of material do not represented in term " Raney catalyst ".The Raney catalyst is owing to higher specific surface area has high activity, and lower temperature is used in permission in hydrogenation.Raney activity of such catalysts metal comprises nickel, copper, cobalt, ferrum, rhodium, ruthenium, rhenium, osmium, iridium, platinum, palladium, their chemical compound and their combination.

Can also in basic Raney metal, add promoter metals and influence Raney selectivity of catalyst and/or activity.The promoter metals that is used for the Raney catalyst can be selected from the transition metal of periodic table of elements group III A to VIIIA, IB and IIB family.The example of promoter metals is chromium, molybdenum, platinum, rhodium, ruthenium, osmium and palladium, is generally about 2% of total weight metal.

The useful catalysts carrier can be any solid, inert substance herein, includes but not limited to oxide such as silicon oxide, aluminium oxide and titanium dioxide; Barium sulfate; Calcium carbonate; And carbon.Catalyst carrier can be powder, granule, ball or analogous shape.

The preferred carrier material of the present invention is selected from carbon, aluminium oxide, silicon oxide, silica-alumina, silicon oxide-titanium dioxide, titanium dioxide, titanium dioxide-aluminium oxide, barium sulfate, calcium carbonate, strontium carbonate, their chemical compound and their combination.Metallic catalyst on the carrier can also have the carrier material of being made by one or more chemical compounds.Preferred carrier is carbon, aluminium oxide and titanium dioxide.Further preferred carrier is that surface area is greater than 100m ²The carbon of/g.Further preferred carrier is that surface area is greater than 200m ²The carbon of/g.Preferably, the content of ashes of carbon is lower than 5% of catalyst carrier weight; Content of ashes is the remaining inorganic residues (percent with original carbon weight is represented) in carbon calcining back.

Available on the market, can be used for carbon of the present invention and comprise those that sell with following trade mark: Bameby﹠amp; Sutcliffe ^TM, Darco ^TM, Nuchar ^TM, Columbia JXN ^TM, Columbia LCK ^TM, Calgon PCB ^TM, Calgon BPL ^TM, Westvaco ^TM, Norit ^TMWith Barnaby Cheny NB ^TMThis carbon can also be available carbon such as Calsicat C on the market, Sibunit C, or Calgon C (can obtain with the trade mark Centaur_ that registers from the market).

In the inventive method, based on the gross weight meter of metallic catalyst weight and vehicle weight, the preferred content of metallic catalyst is about 0.1% to about 20% of a supported catalyst in the supported catalyst.Preferred metal catalyst content is about 1% to about 10% of a catalyst on the carrier.Further preferred metal catalyst content is about 3% to about 7% of a catalyst on the carrier.

The combination of catalyst and carrier system can comprise any one metal shown in this article and any one carrier shown in this article.The combination of preferred catalyst and carrier comprises the palladium on the carbon, palladium on the calcium carbonate, palladium on the barium sulfate, palladium on the aluminium oxide, palladium on the titanium dioxide, palladium on the silicon oxide, platinum on the carbon, platinum on the aluminium oxide, platinum on the silicon oxide, iridium on the silicon oxide, iridium on the carbon, iridium on the aluminium oxide, rhodium on the carbon, rhodium on the silicon oxide, rhodium on the aluminium oxide, nickel on the carbon, nickel on the aluminium oxide, nickel on the silicon oxide, rhenium on the carbon, rhenium on the silicon oxide, rhenium on the aluminium oxide, ruthenium on the carbon, ruthenium on the aluminium oxide, ruthenium on the silicon oxide and their combination.

The more preferably combination of catalyst and carrier comprises palladium, the palladium on the aluminium oxide, the palladium on the titanium dioxide, the ruthenium on the carbon, the ruthenium on the aluminium oxide, the rhodium on the carbon, the rhodium on the aluminium oxide, the platinum on the carbon and their combination on the carbon.

The useful levulic acid of the inventive method can utilize the conventional chemical method to obtain, and perhaps obtains based on the reproducible cellulosic material of biology.Compare with conventional method, utilize to be derived from the manufacturing cost that biological levulic acid might reduce The compounds of this invention.

The chemical compound for preparing in the inventive method shows the performance that is applicable in the multiple application.Have N-alkyl pyrrolidone up to the alkyl chain of about 8 carbon atoms as non-proton chemical solvent, littler than other solvent toxicity.The carbochain of N-low alkyl group ketopyrrolidine is not enough to long to can form micelle in water; Therefore these chemical compounds do not have the performance of tangible surfactant.Have about C ₈To C ₁₄The N-alkyl pyrrolidone of alkyl has the performance of surfactant, and the ketopyrrolidine that has longer N-alkyl chain is as chelating agent.U.S. Patent No. 5,294,644 have described some surface active property such as dissolubility, wettability, viscosity potentiation, emulsifying and the complexing of alkyl pyrrolidone.The N-alkyl pyrrolidone can also be used for concentrating colloidal solid.Because their solvent, surfactant and complex performance, so ketopyrrolidine is highly suitable for making medicine, personal-care supplies and industry, agricultural and household chemical product product.

The ketopyrrolidine of the inventive method preparation is applicable to that preparation is used for the medicine of human body, animal, reptile and fish.Ketopyrrolidine disclosed herein is specially adapted to topical formulations, as ointment, cream, lotion, paste, gelinite, spray, aerosol, lotion, shampoo, foam, cream, gelinite, ointment, ointment, milk, paster, spray, face cream, emulsion, powder, solid or liquid soap or oil.Ketopyrrolidine can be used for promoting the active component transdermal flux to human body or animal tissue and system as the 5-N-methyl-2-2-pyrrolidone N-.Ketopyrrolidine can also be used as solubilizing agent, improves the dissolubility of treatment preparation in carrier system.

The ketopyrrolidine of the inventive method preparation can also be tied into matrix system, as paster, is used for for example percutaneous dosing of antibacterial, hormone or anti-inflammatory agent.The preparation of drug combination method that pharmacy industry adopts usually is useful for the inventive method.For the argumentation of this method, referring to, for example Remington ' s Pharmaceutical Sciences (AR Gennaro, ed., 20 ^ThEdition, 2000, Williams﹠amp; Wilkins, PA), the document is introduced into this paper for your guidance.

The ketopyrrolidine of the inventive method preparation can be as solvent or surfactant in liquid, gelinite or aerosol cleaning combination, described cleaning combination is used to clean kinds of surface, comprise textile such as clothes, fabric and carpet and crust such as glass, metal, pottery, porcelain, synthetic plastic and porcelain enamel.Ketopyrrolidine can also be used for preparation, and described preparation is used for crust as house or public organizations or hospital environment, perhaps is used for skin surface, or fabric face, or food production, restaurant or hotel.In addition, Cleasing compositions is useful in the removal of industrial dirt such as dirt, oils and fats, oil, China ink etc.Ketopyrrolidine can also be used on goods or the manufacturing equipment cleaning, solvation and/or remove resin or the compositions of polymer is used as solvent.

Except ketopyrrolidine, can comprise other component in the Cleasing compositions.These other components comprise non-ionic surface active agent, anion surfactant, cationic surfactant, amphoteric surfactant and solvent.Illustrative non-ionic surface active agent is an alkylpolyglycosides, as Glucopon (Henkel Corporation), the oxirane of alkyl phenol and blended ethylene oxide/propylene oxide addition product, the oxirane of long-chain alcohol or fatty acid and blended ethylene oxide/propylene oxide addition product, blended ethylene oxide/propylene oxide block copolymer, ester such as dehydrated sorbitol mono-fatty acid ester, the alkanolamide etc. of fatty acid and hydrophilic alcohol.

Illustrative anion surfactant is a soap, contains the senior alkyl benzene sulfonate of 9 to 16 carbon atoms in the senior alkyl of straight or branched, C ₈To C ₁₅Alkyl toluene sulfonate, C ₈To C ₁₅Alkyl phenol sulfonate, alkene sulfonate, paraffin sulfonate, the sulfate of pure and mild alcohol ether, phosphate ester etc.

Illustrative cationic surfactant comprises amine, amine oxide, and the alkylamine ethoxy compound, the ethylenediamine alkoxide compound is as the Tetronic_ series from BASF Corporation, quaternary amine etc.

Illustrative amphoteric surfactant is not only to have had acid in its structure but also have those of basic group, as amino and carboxyl, or amino and sulfonic group, or amine oxide etc.Suitable amphoteric surfactant comprises betanin, sulfobetaines, imidazoline etc.

Illustrative solvent comprises glycol, glycol ethers, aliphatic alcohol, alkanolamine, ketopyrrolidine and water.

This surfactant and solvent are described in, McCutcheon ' s (2002) for example, Volume1 (Emulsifiers and Detergents) and Volume 2 (Functional Materials), The Manufacturing Confectioner Publishing Co., Glen Rock, NJ.

Cleasing compositions can also comprise other composition, as chelating agen, antiseptic, antimicrobial compound, buffer agent and pH regulator agent, spice, dyestuff, enzyme and bleach.

N-alkyl-2-Pyrrolidone is useful in cleaning and demoulding preparation, is used for removing (or peeling off) photoresist film (or other similar organic polymer films) or layer from substrate, perhaps removes or clean various types of plasma etching residues from substrate.N-alkyl-2-Pyrrolidone is useful removing from printing spreader and circuit bank accessory the cleaning formulation of deflux as surfactant also.

N-alkyl-2-Pyrrolidone, as 5-methyl-N-octyl group-2-Pyrrolidone and 5-methyl-N-dodecyl-2-Pyrrolidone, can be used as the component of jetted ink, to improve antagonism high light hangover property when being printed as image, produce evenly printing (minimizing degree of carrying secretly), and give improved color fastness to water and/or better dried or wet friction.2-Pyrrolidone such as 5-methyl-N-cyclohexyl-2-Pyrrolidone or 5-methyl-N-N-methyl-2-2-pyrrolidone N-can also prepare as solvent at hot melt that is used for colored printing or phase change ink.

The ketopyrrolidine of the inventive method preparation can also be used to make agricultural chemicals, includes but not limited to herbicide, insecticide, antifungal, antibacterial, nematicide, algicide, mulluscicides, antiviral, makes plant produce repellent medicine and plant growth regulator or their mixture of chemical compound, bird, animal and the insecticide of resistance.Preparation method comprises at least a ketopyrrolidine of agrochemicals effective agents well known by persons skilled in the art with any means of the present invention preparation is contacted.Agricultural chemical composition can randomly comprise other auxiliary element commonly used in the agricultural chemicals industry.

Ketopyrrolidine as 5-methyl-N-Methyl pyrrolidone and 5-methyl-N-cyclohexyl-ketopyrrolidine, can be used as water-fast polar latent solvent, dissolving water-fast pesticide and other agricultural chemicals, and increases the amount of active component.The N-alkyl pyrrolidone, preferred N-C _3-15Alkyl pyrrolidone, especially 5-methyl-N-octylpyrrolidone and 5-methyl-N-dodecyl pyrrolidone can be used as non-ionic surface active agent, and be auxiliary as emulsifying agent.Use plant growth regulator to improve the economic flow rate of crops.5-methyl-N-octylpyrrolidone and 5-methyl-N-dodecyl pyrrolidone can be made solvent and use in containing the emulsion of plant growth regulator.

In addition, ketopyrrolidine can be used for liquid or aerosol preparations, is used for the insect repellant medicine that applies on people's the skin, and example comprises mosquito and tick repellent medicine.The preparation of this insect repellant medicine comprises that at least a insect repellent with effective dose contacts with at least a product that utilizes at least a the inventive method preparation.

Ketopyrrolidine, for example 5-methyl-N-N-methyl-2-2-pyrrolidone N-can also be used for the animal ensilage and store used anti-microbial agents.

As the part that the environmental consciousness method is more arranged, 5-methyl-N-alkyl-2-Pyrrolidone can also be used for dry-cleaning of garments, and it comprises the carbon dioxide of surfactant and enrichment, substitutes conventional solvent.

In addition, the 5-N-methyl-2-2-pyrrolidone N-can also be with the component in the protective composite that acts on lacquered surface such as automobile.Ketopyrrolidine is used for wetted surface and improves protectant spreadability.

Different plastic materials is non-miscible often, makes product show insufficient mechanical performance.The chemical compound that contains monomer and polymeric 5-methyl-ketopyrrolidine can be as the bulking agent of plastics composite; Bulking agent makes it itself to be connected on the interface between the contained polymer, perhaps infiltrates in the polymer, has improved the bonding force between the polymer thus and has improved mechanical performance.

5-methyl-N-ketopyrrolidine can also be made bulking agent in refrigeration and air-conditioning industry.Because with the soluble mixcibility of conventional lubricant such as mineral oil, poly alpha olefin and alkylbenzene, therefore at the lubricant that just is necessary by Chlorofluorocarbons (CFCs) to the transition of hydrofluoroalkane cold-producing medium to use a class new.Yet, the expensive and very easy moisture absorption of the lubricant that this class is new.Absorbing water causes generating acid and corrosion refrigeration system and forms mud.Hydrofluoroalkane deficiency of dissolubility in conventional lubricant causes forming very heavy-gravity lubricant at non-compressor section, and causes lubricant can not fully return compressor.This finally may produce some problems, comprises overheat of compressor and block in (seizing) and the refrigeration system heat exchange insufficient.At non-compressor section, bulking agent has dissolved polarity halogenate hydrocarbon refrigerant and traditional nonpolar lubricant, makes lubricant return compressor section efficiently.Bulking agent can comprise 5-methyl-N-alkyl-and 5-methyl-N-cycloalkyl-2-Pyrrolidone.

Ketopyrrolidine can also be used as the fuel and lubricant additive.For example, N-alkyl-2-Pyrrolidone can be used as cleaning agent and dispersant in fuel additive composition, to keep valve, carburetor and injecting systems cleaning, improve combustion characteristics thus and reduced precipitate, so just reduced the discharging of air pollutants.In addition, 5-methyl-N-N-methyl-2-2-pyrrolidone N-can be used for crude lube stock remaining after former lube cut or the depitching and remove unsaturated hydrocarbons, to prepare solvent-refined crude oil as lubricant.

To those skilled in the art, preparation method right and wrong Changshu of cleaning, demoulding, agricultural chemicals and plastic formulation is known.Equally, protectiveness preparation, fuel additive and the lubricant of insect repellent, jetted ink, paint, refrigeration and air-conditioning method for preparing lubricant and dry-cleaning method in this area also right and wrong Changshu know.Ketopyrrolidine can be used as solvent, surfactant, dispersant, cleaning agent, emulsifying agent, viscosity synergist and chelating agent in these preparations.Select suitable ketopyrrolidine based on standard screening method to properties of product.Other composition such as medicine or agrochemicals activating agent or coloring agent can be used as main function ingredients and join in the concrete preparation; The performance of function ingredients will be by concrete purposes decision.Can also add and improve or for the helper component of preparation effect key.Helper component can comprise solvent or cosolvent, thickening agent, antioxidant, spreading agent, antiseptic, binding agent, emulsifying agent, defoamer, wetting agent, dispersant, surfactant, suitable carriers, matrix system, delivery vehicles, spice, salt, ester, amide, alcohol, ether, ketone, acid, alkali, alkane, siloxanes, evaporation regulator, paraffin, aliphatic hydrocarbon or aromatic hydrocarbons, chelating agen, be used for aerosol, propellant or the gas that is used to dry-clean, You Heshui.Suitable auxiliary agents component to purposes described herein is well known by persons skilled in the art.

The following examples are used to illustrate the present invention.Embodiment 1 to 29 is the embodiment of existing (reality), and embodiment 30 to 35 indicates.

Embodiment

Used abbreviation is as follows:

ESCAT-XXX:Engelhard Corp. (Iselin, the series catalyst that NJ) provides

JM-AXXXX, Johnson Matthey, (W.Deptford NJ) provides Inc.

JM-XXXX-SA, series catalyst

JM-XXXX，

JM-BXXXX：

Calsicat carbon: the catalyst that provides by Engelhard Corp. (lot S-96-140)

Carrier

SCCM: standard cubic centimeter per minute

GC: vapour phase chromatograph

GC-MS: vapour phase chromatography-mass spectroscopy

During the preparation catalyst, commercially available carrier such as carbon, aluminium oxide, silicon oxide, silica-alumina or titanium dioxide are flooded with slaine beginning profit.The catalyst system therefor precursor is NiCl ₂6H ₂O (Alfa Chemical Co., Ward Hill, MA), Re ₂O ₇(Alfa ChemicalCo.), PdCl ₂(Alfa Chemical Co.), RuCl ₃XH ₂O (Aldrich Chemical Co., Milwaukee, WI), H ₂PtCl ₆(Johnson Matthey, Inc.) and RhCl ₃XH ₂O (AlfaChemical Co.).With sample drying and under 300 to 450 ℃ and hydrogen reductase 12 hour.

The Raney catalyst derives from W.R.Grace﹠amp; Co. (Columbia, MD), and allyl acetonitrile, benzene nitrile, diox and levulic acid derive from Fisher Scientific (Chicago, IL).

Preparation of Catalyst: the 5%Pt on the pickling Calsicat carbon

In the 150ml beaker, solution is by 4.5ml 0.3M H ₂PtCl ₆Form with the 4.0ml deionized water.In beaker, add 4.75gCalsicat acid-washed carbon (12 * 20 orders, 120 ℃ of following dried overnight).Once in a while under the stirring condition, will place 1 hour under the slurry room temperature, then under frequent stirring condition, 120 ℃ of following dried overnight (up to free-flow).

Catalyst is placed in the alumina boat, places the tube furnace of quartz liners, use 500SCCM N ₂Purged 15 minutes under the room temperature, then with purging 15 minutes under the 100SCCM He room temperature.This catalyst is heated to 150 ℃, and remained on 150 ℃ of He following 1 hour.At this moment, add 100SCCMH ₂, and sample remained on 150 ℃ He and H ₂Following 1 hour.Temperature is elevated to 300 ℃, makes the He-H of catalyst under 300 ℃ ₂Under reduced 8 hours.Stop to add H ₂, and sample remained on following 30 minutes of He under 300 ℃, cool to room temperature in He stream then.At last, with catalyst at room temperature 500SCCM contain 1.5%O ₂N ₂Middle passivation 1 hour is weighed as 4.93g after the discharging.

Other used catalyst of the present invention prepares according to similar approach.

Levulic acid (LA) be reduced in batches 5-methyl-N-(methyl aryl)-2-Pyrrolidone and 5-methyl- N-(methyl cycloalkyl)-2-Pyrrolidone

Adding 50gm catalyst and 1gm contain the solution of 35wt% levulic acid, 31% aryl cyano compound and 34% diox in the 5ml high-pressure bottle.With seal of vessel, charge into 5.52MPa hydrogen, and be heated to 150 ℃ of maintenances 4 hours.In the course of reaction, pressure is remained under the 5.52MPa.When reaction finished, with container cooling fast in ice, aerofluxus also added target methyl ethyl ether in the GC.With pipet separation solution from catalyst, and utilize the HP 6890 that FFAP 7717 (30 meters) post has been installed to analyze by GC-MS.The result who provides in the following table is based on area %.

Below described embodiment carry out under the condition that provides for each embodiment according to similar approach.

Embodiment 1-25

Utilize levulic acid (LA) and 3 pentene nitrile (3PN) preparation 5-methyl-N-pentylidene-2-pyrrole Pyrrolidone (PeMP)

The embodiment numbering	Catalyst/support a	Time (hrs)	Temperature (C)	H 2Pressure (MPa)	Raw material (wt%:35/25/40)	PeMP productive rate (%)
							1	5％Pd/C(JM-A503023-5)	6	150	6.90	LA/3PN/H 2O	0.7
2	5％Pd/C(ESCAT-142)	6	150	6.90	LA/3PN/H 2O	0.2
							3	5％Pd/C(JM-A11108-5)	6	150	6.90	The LA/3PN/ diox	13.5
4	5％Pd/C(ESCAT-142)	6	150	6.90	The LA/3PN/ diox	21.8
							5	5％Ru/C(Aldrich)	6	150	6.90	The LA/3PN/ diox	28.9
6	5％Pd/C(JM-A1 1108-5)+ 5％Ru/Calsicat C	6	150	6.90	The LA/3PN/ diox	30.7
							7	5％Pd/C(ESCAT-142)+ 5％Ru/Calsicat C	6	150	6.90	The LA/3PN/ diox	31.8
8	5％Ru/C(JM-141060-SA)	6	150	5.52	The LA/3PN/ diox	22.5
							9	5％Ru/Al 2O 3(Aldrich)	6	150	5.52	The LA/3PN/ diox	28.7
10	5％Rh/C(JM-11761)	6	150	5.52	The LA/3PN/ diox	28.6
							11	5％Rh/Al 2O 2(Aldrich)	6	150	5.52	The LA/3PN/ diox	41.4
12	5％Pt/C(JM-B21142-5)	6	150	5.52	The LA/3PN/ diox	5.4
							13	5％Pt/C(ESCAT-248)	6	150	5.52	The LA/3PN/ diox	7.7
14	5％Pt/C(ESCAT-294)	6	150	5.52	The LA/3PN/ diox	33.1
							15	5％Pd/C(JM-A11108-5)	2+4	75+150	5.52	The LA/3PN/ diox	10.8
16	5％Pd/Al 2O 3(JM-A22117- 5)	2+4	75+150	5.52	The LA/3PN/ diox	36.2
							17	5％Ru/C(JM-141060-SA)	2+4	75+150	5.52	The LA/3PN/ diox	34.2
18	5％Ru/Al 3O 3(Aldrich)	2+4	75+150	5.52	The LA/3PN/ diox	28.6
							19	5％Rh/C(JM-11761)	2+4	75+150	5.52	The LA/3PN/ diox	26.9
20	5％Rh/Al 2O 3(Aldrich)	2+4	75+150	5.52	The LA/3PN/ diox	43.4
							21	5％Pt/C(JM-B21101-5)	2+4	75+150	5.52	The LA/3PN/ diox	6.3
22	5％Ru/C(JM-141060-SA) +5％Pd/C(ESCAT-142)	2+4	75+150	5.52	The LA/3PN/ diox	6.5
							23	5％Ru/Al 2O 3(Aldrich)+ 5％Pd/C(ESCAT-142)	2+4	75+150	5.52	The LA/3PN/ diox	36.5
24	5％Rh/C(JM-11761)+5％ Pd/C(ESCAT-142)	2+4	75+150	5.52	The LA/3PN/ diox	6.3
							25	5％Rh/Al 2O 3(Aldrich)+ 5％Pd/C(ESCAT-142)	2+4	75+150	5.52	The LA/3PN/ diox	27.9

^aThe source of the commercially available catalyst/support that gets is in bracket.

Embodiment 26-29

Utilize levulic acid (LA) and benzonitrile (BN) preparation 5-methyl-N-benzyl-2-pyrrolidine Ketone (BzMP) and 5-methyl-N-(methylcyclohexyl)-2-Pyrrolidone (CHMMP)

Response time is 4 hours.Temperature and pressure is respectively 150 ℃ and 5.52MPa.The results are shown in the following table.

The embodiment numbering	Catalyst/support a	Raw material (wt%:35/31/36)	LA conversion ratio (%)	BzMP selectivity (%)	CHMMP selectivity (%)
						26	5％Pd/C(ESCAT-142)	The LA/BN/ diox	85.8	48.2	0.5
27	5％Pt/C(ESCAT-248)	The LA/BN/ diox	79.4	22.1	0.7
						28	5％Rh/C(JM-11761)	The LA/BN/ diox	98.2	1.9	0.0
29	5％Ru/C(ESCAT-440)	The LA/BN/ diox	100.0	1.5	0.2

^aThe source of the commercially available catalyst/support that gets is in bracket.

Embodiment 30: pharmaceutical preparation

A) topical formulations:

Solubilizing agent (diethylene glycol monoethyl ether) 2% to 50%

Dermal osmosis accelerator (N-ethoxy-2-Pyrrolidone) 2% to 50%

Emulsifying agent 2% to 20%

Emollient (propylene glycol) 2% to 20%

Antiseptic 0.01 to 0.2%

Activator 0 to 25%

The carrier surplus

B) cream

The 1st phase:

Polyethylene Glycol and stearic acid palm fibre eleostearic acid glycol ester 5%

Caprylic/capric triglyceride 5%

Oleoyl polyethyleneglycol glyceride (Labrafil M 1944CS) 4%

Spermol 5.5%

PPG-2 myristicin propionic ester (Crodamol PMP) 6%

5-methyl-N-ethoxy-2-Pyrrolidone 2%

The 2nd phase

Xanthan gum 0.3%

Pure water 55%

The 3rd phase

Propylene glycol 1%

Methyl parahydroxybenzoate 0.18%

Propyl p-hydroxybenzoate 0.02%

The 4th phase

Naftifine hydrochloride (antifungal) 1%

Diethylene glycol monoethyl ether (Transcutol) 15%

Method

Disperse yellow virgin rubber and leaving standstill in water.Respectively the 1st phase component and the 2nd phase component are heated to 75 ℃; Sneak into the 2nd phase mutually with the 1st under the high-speed stirred.Temperature is remained on 75 ℃ to be descended and stirred 10 minutes.Mixture is slowly cooled off stirring at low speed the time then.Add the 3rd phase in the time of 40 ℃.Then naftifine is fully sneaked among the Transcutol, and mixture is added cream, fully mix, the cream cool to room temperature.

C) dermal osmosis patch formulation

Ketoprofen 0.3%

Polysorbate 80 0.5%

5-methyl-N-N-methyl-2-2-pyrrolidone N-1%

5-methyl-N-ethyl-2-pyrrolidone 2%

Polyethylene Glycol (PEG) 400 10%

Sodium carboxymethyl cellulose (CMC-Na) 4%

Sodium polyacrylate 5.5%

Sanwet 1M-1000PS 0.5％

Polyvinyl alcohol 1%

PVP/VA copolymer 3%

Embodiment 31: Cleasing compositions

A) remove lubricating oil preparation

Water 89%

Potassium carbonate 1%

Potassium bicarbonate 5%

5-methyl-N-octyl group-2-Pyrrolidone 2.5%

Deriphatec 151-C(Henkel Corp.) 2.5％

B) O/w emulsion of aerosol form

Crillet 45(Croda) 3.30％

Monamulse DL 1273(Mona Industries，Inc.) 3.30％

5-methyl-N-dodecyl-2-Pyrrolidone 5.50%

Degeneration dehydrated alcohol 100AG/F3 (CSR Ltd) 15.40%

Norpar15(Exxon) 5.50％

Deionized water 44.10%

Butane 16.95%

Propane 5.95%

C) general liquid cleansing composition

Neodol 91-8(Shell) 3.5％

Straight chained alkyl (C _9-13) benzene sulfonate, magnesium salt 10.5%

Propylene glycol list tertbutyl ether 4.0%

Fatty acid distribution of coconut oil 1.4%

5-methyl-N-decyl-2-Pyrrolidone 1.0%

Bitter salt 5.0%

Water 74.6%

D) shower compositions

Glucopon 225(Henkel Corp.) 2.0％

Isopropyl alcohol 2.2%

Sequestrene 40 (edta and its sodium salt) 1.0%

(45％，Ciba)

Spice 0.02%

Barquat 4250Z(50％，Lonza) 0.2％

5-methyl-N-octyl group-2-Pyrrolidone 1.0%

Water 93.58%

E) compositions that washes the dishes

Ethanol (95%) 8.6%

Alfonic 1412-A[oxirane sulfate (59.3%)] 22.5%

Alfonic 1412-10 1.1％

Sodium chloride 0.9%

5-methyl-N-decyl-2-Pyrrolidone 7.5%

Water 59.4%

F) waterborne antibacterial Cleasing compositions

Adipic acid 0.40%

Dacpon 27-23AL (Condea; C _12-14Alkyl sodium sulfate, 0.15%

Active 28%)

Isopropyl alcohol 1.8%

Dowanol PnB (Dow; Propylene glycol list-N-butyl ether) 0.30%

5-methyl-N-octyl group-2-Pyrrolidone 0.4%

Sodium hydroxide 0.05%

Water 96.9%

Substrate can be prepared Antibacterial rag with the above-mentioned composition dipping; Substrate can be to comprise that ratio is that 70: 30 viscose glue/polyester and proportion is 50g/m ²Spunlaced fabric.About 2.6: 1 of the ratio of compositions and substrate.

G) disinfectant

Benzalkonium chloride 5%

Sodium carbonate 2%

Sodium citrate 1.5%

Nonoxinol 10 2.5%

5-methyl-N-octyl group-2-Pyrrolidone 5%

Water 84%

H) antiparasitic (being used for animal skin applies)

Antiparasitic 1 to 20%

5-methyl-N-isopropyl propyl group-2-Pyrrolidone 30%

Benzyl alcohol (antiseptic) 3%

Thickening agent 0.025-10%

Coloring agent 0.025-10%

Emulsifying agent 0.025-10%

Water surplus

Embodiment 32: demoulding/cleaning formulation

5-methyl-N-N-methyl-2-2-pyrrolidone N-30%

Monoethanolamine 55%

Lactic acid 5%

Water 10%

Embodiment 33: jetted ink

CAB-O-JET 300 (active) 4%

Diethylene glycol 17.5%

5-methyl-N-octyl group-2-Pyrrolidone 2.5%

Deionized water 76%

Embodiment 34: agricultural chemical composition

A) be used to control the compositions of insecticide

Permethrin 2%

5-methyl-N-decyl-2-Pyrrolidone 3%

Dimethyl dipropyl naphthalene 7%

Lauryl alcohol 5%

Hymal 1071(Matsumoto Yushi Seiyaky， 10％

Inc.)

Hytenol N-08(Daiichi Kogyo Seiyaku，Inc.) 2％

Polyoxyethylene glycol 71%

B) pesticidal preparations

5-methyl-N-alkyl pyrrolidone 48%

Sodium lauryl sulphate 12%

Agrimer AL25 10％

Rodeo (pesticide; Monsanto) 1%

Water 29%

C) emulsible fungicide preparation

Kresoxin-methyl 0.5％

Propylene carbonate 1.5%

Aromatics petroleum distillate 150 (Exxon) 2.9%

5-methyl-N-octyl group-2-Pyrrolidone 3.8%

Contain 50% (dodecane 1.4% among the CaH/DDBSA[Exxon 150

Base benzenesulfonic acid calcium+DBSA (5: 1))]

Water surplus

Embodiment 35: the preparation of the protective composite of the car surface that is used to spray paint

Propylene glycol phenylate 2.0%

5-methyl-N-octyl group-2-Pyrrolidone 0.1%

Emulsifying siloxanes: 3.0%

A) dimethyl siloxane (2.67%)

B) aminofunctional siloxanes (0.21%)

C) silicone resin (0.12%)

Water 94.9%

Claims (21)

1. preparation contains the method for the product of 5-methyl-(N-methyl aryl)-2-Pyrrolidone (III), 5-methyl-N-(methyl cycloalkyl)-2-Pyrrolidone or its mixture, this method is included in hydrogen and catalyst exists down, the step that levulic acid (I) is contacted with aryl cyano compound (II), catalyst is optional to be supported on the catalyst carrier, and randomly, described contact is carried out in the presence of solvent;

Wherein, R ₁Be aryl with 6 to 30 carbon atoms, R ₂Be R ₁All or part of reductive deriveding group.

2. preparation contains the method for the product of 5-methyl-N-alkyl-2-Pyrrolidone (VI), this method is included in hydrogen and catalyst exists down, the step that levulic acid (I) is contacted with alkyl cyanide based compound (V), catalyst is optional to be supported on the catalyst carrier, and randomly, described contact is carried out in the presence of solvent;

Wherein, R ₃Be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀The alkenyl, the C that do not replace or replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀The cycloalkyl that does not replace or replace or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace.

3. claim 1 or 2 method, wherein catalyst is selected from nickel, copper, cobalt, ferrum, rhodium, ruthenium, rhenium, osmium, iridium, platinum, palladium, at least a Raney metal; Their chemical compound; With their combination.

4. the method for claim 3, wherein catalyst is supported forming the metallic catalyst on the carrier, and the content in the metallic catalyst of metal on carrier is 0.1wt% to 20wt%.

5. the method for claim 3, wherein catalyst carrier is selected from carbon, aluminium oxide, silicon oxide, silica-alumina, silicon oxide-titanium dioxide, titanium dioxide, titanium dioxide-aluminium oxide, barium sulfate, calcium carbonate, strontium carbonate, their chemical compound and their combination.

6. the method for claim 5, wherein carbon has content of ashes, and this content of ashes is lower than about 5wt% of catalyst carrier, and randomly, wherein the surface area of carbon is greater than about 200m ²/ g.

7. claim 1 or 2 method, wherein this method is randomly to carry out in the presence of promoter.

8. the process of claim 1 wherein R ₁Be aryl with 6 to 12 carbon atoms, and R wherein ₂It is cycloalkyl with 6 to 12 carbon atoms.

9. the method for claim 2, wherein R ₃It is alkyl or cycloalkyl with 1 to 12 carbon atom.

10. claim 1 or 2 method, wherein during the reaction beginning, R ₁-CN/ levulic acid and R ₃The ratio of-CN/ levulic acid is about 0.01/1 to about 100/1.

11. the method for claim 10, wherein reaction is to carry out to about 300 ℃ temperature at about 25 ℃.

12. the method for claim 10, wherein reaction is to carry out to the Hydrogen Vapor Pressure of about 20.00MPa at about 0.34MPa.

13. the method for claim 4, wherein the metallic catalyst on the carrier is selected from palladium, the palladium on the calcium carbonate, the palladium on the barium sulfate, the palladium on the aluminium oxide, the palladium on the titanium dioxide, the platinum on the carbon, the platinum on the aluminium oxide, the platinum on the silicon oxide, the iridium on the silicon oxide, the iridium on the carbon, the iridium on the aluminium oxide, the rhodium on the carbon, the rhodium on the silicon oxide, the rhodium on the aluminium oxide, the nickel on the carbon, the nickel on the aluminium oxide, the nickel on the silicon oxide, the rhenium on the carbon, the rhenium on the silicon oxide, the rhenium on the aluminium oxide, the ruthenium on the carbon, the ruthenium on the aluminium oxide and the ruthenium on the silicon oxide on the carbon.

14. the method for claim 13, wherein the metallic catalyst on the carrier is selected from palladium, the palladium on the aluminium oxide, the palladium on the titanium dioxide, the ruthenium on the carbon, the ruthenium on the aluminium oxide, the rhodium on the carbon, the rhodium on the aluminium oxide, the platinum on the carbon and their combination on the carbon.

15. the method for claim 1 or 2, wherein Fan Ying solvent medium is selected from the product of cyano compound, ketopyrrolidine and claim 1 or 2 of water, alcohol, ether, formula (II) or formula V respectively.

16. the method for claim 2, wherein R ₃It is alkyl with 1 to 12 carbon atom, or has a cycloalkyl of 6 to 12 carbon atoms, wherein catalyst is on the carrier, and supported catalyst is palladium on the carbon or the palladium on the titanium dioxide, and wherein reaction temperature is about 75 ℃ to 200 ℃, and reaction pressure is that about 1.3MPa is to about 7.6MPa.

17. the method for pharmaceutical compositions, this method comprises the steps:

I) utilize following method to prepare 5-methyl-N-alkyl-2-Pyrrolidone (VI), this method is included in hydrogen and metallic catalyst exists down, metallic catalyst is optional to be supported catalyst, and randomly, in the presence of solvent, the step that levulic acid (I) is contacted with alkyl cyanide based compound (V);

Wherein: R ₃Be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀Do not replace or

The alkenyl, the C that replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀Do not replace or

The cycloalkyl that replaces or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace; With

Ii) 5-methyl-N-alkyl-2-Pyrrolidone (VI) is contacted with at least a rem.

18. prepare the method for agricultural chemical composition, this method comprises the steps:

I) utilize following method to prepare 5-methyl-N-alkyl-2-Pyrrolidone (VI), this method is included in hydrogen and metallic catalyst exists down, metallic catalyst is optional to be supported catalyst, and randomly, in the presence of solvent, the step that levulic acid (I) is contacted with alkyl cyanide based compound (V);

Wherein: R ₃Be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀Do not replace or

The alkenyl, the C that replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀Do not replace or

The cycloalkyl that replaces or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace; With

Ii) 5-methyl-N-alkyl-2-Pyrrolidone (VI) is contacted with at least a agricultural effective agent.

19. prepare the method for Cleasing compositions, this method comprises the steps:

I) utilize following method to prepare 5-methyl-N-alkyl-2-Pyrrolidone (VI), this method is included in hydrogen and metallic catalyst exists down, metallic catalyst is optional to be supported catalyst, and randomly, in the presence of solvent, the step that levulic acid (I) is contacted with alkyl cyanide based compound (V);

Wherein: R ₃Be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀The alkenyl, the C that do not replace or replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀The cycloalkyl that does not replace or replace or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace; With

Ii) with 5-methyl-N-alkyl-2-Pyrrolidone (VI) be selected from following chemical compound and contact: anion surfactant, non-ionic surface active agent, cationic surfactant, amphoteric surfactant, glycol, glycol ethers, aliphatic alcohol, alkanolamine, ketopyrrolidine, water and their mixture.

20. prepare the method for inkjet ink composition, this method comprises the steps:

I) utilize following method to prepare 5-methyl-N-alkyl-2-Pyrrolidone (VI), this method is included in hydrogen and metallic catalyst exists down, metallic catalyst is optional to be supported catalyst, and randomly, in the presence of solvent, the step that levulic acid (I) is contacted with alkyl cyanide based compound (V);

Wherein:

R ₃Be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀The alkenyl, the C that do not replace or replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀The cycloalkyl that does not replace or replace or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace; And

Ii) 5-methyl-N-alkyl-2-Pyrrolidone (VI) is contacted with at least a coloring agent.

21. prepare the method for cold-producing medium or air-conditioning lubricating oil, this method comprises the steps:

I) utilize following method to prepare 5-methyl-N-alkyl-2-Pyrrolidone (VI), this method is included in hydrogen and metallic catalyst exists down, metallic catalyst is optional to be supported catalyst, and randomly, in the presence of solvent, the step that levulic acid (I) is contacted with alkyl cyanide based compound (V);

Wherein: R ₃Be C ₁-C ₃₀The alkyl, the C that do not replace or replace ₁-C ₃₀The alkenyl, the C that do not replace or replace ₁-C ₃₀The alkynyl, the C that do not replace or replace ₃-C ₃₀The cycloalkyl that does not replace or replace or contain at least one heteroatomic C ₃-C ₃₀The cycloalkyl that does not replace or replace; And

Ii) 5-methyl-N-alkyl-2-Pyrrolidone (VI) is contacted with at least a cold-producing medium.